Chemistry - A European Journal p. 18216 - 18224 (2017)
Update date:2022-08-16
Topics:
Werther, Philipp
M?hler, Jasper S.
Wombacher, Richard
Bioorthogonal reactions have emerged as a versatile tool in life sciences. The inverse electron demand Diels–Alder reaction (DAinv) stands out due to the availability of reactants with very fast kinetics. However, highly reactive dienophiles suffer the disadvantage of being less stable and prone to side reactions. Herein, we evaluate the extent of acceleration of rather unreactive but highly stable dienophiles by DNA-templated proximity. To this end, we developed a modular synthetic route for a novel bifunctional fluorogenic tetrazine rhodamine probe that we used to determine the reaction kinetics of various dienophiles in a fluorescence assay. Under proximity-driven conditions the reaction was found to be several orders of magnitude faster, and we observed almost no background reaction when proximity was not induced. This fundamental study identifies a minimally sized fluorogenic tetrazine dienophile reactant pair that has potential to be generally used for the visualization of biomolecular interactions with temporal and spatial resolution in living systems.
View MoreContact:+86-10-59484199
Address:No.58-A1026 Liangguan Street
NIGNXIA XINDACHANG TECHNOLOGY CO.,LTD
website:https://xdcchemical.com/
Contact:86-311-85758226
Address:North Industry Area, Wuji
Engineering Research Center of Pesticide, Heilongjiang Province
Contact:+86-451-86609001
Address:No.74 of Xuefu Road, Nangang District,
website:http://www.shengmaochem.com
Contact:86-27-82853423, 82819281
Address:Rm 202, A Unit Huaqiao Building No. 2, Lihuangpi Road, Wuhan, China
Tianjin Ingenochem Technology Co.,Ltd
Contact:+86-22-23677060
Address:Hitech Green Industry Park K2-9-602, Nankai district
Doi:10.1039/c4cc06132b
(2014)Doi:10.1016/S0040-4020(98)01070-9
(1999)Doi:10.1002/ejoc.201300307
(2013)Doi:10.1039/b604591j
(2006)Doi:10.1080/00397919608003721
(1996)Doi:10.3390/10010302
(2005)